Synthesizing method of indole and indolizine ketone compounds

A technology of indolizinone and synthesis method, applied in the direction of organic chemistry and the like, can solve problems such as no literature report, and achieve the effects of rich variety, concise and efficient synthesis method, and wide adaptability of substrates

Inactive Publication Date: 2019-05-31
HUAIHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] There are many types of indolezine derivatives, and the synthesis of indolezine derivatives has been reported in the literature, but for the use of β-indoleamine and β-buty

Method used

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  • Synthesizing method of indole and indolizine ketone compounds
  • Synthesizing method of indole and indolizine ketone compounds
  • Synthesizing method of indole and indolizine ketone compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] The reaction formula is:

[0019]

[0020] Add 10mmol (5-methyl-1H-indol-3-yl)methanamine, 12mmol 3-pentynoic acid and 10mL ionic liquid [BMIm]Br into the reaction flask, stir until dissolved, then add 0.5mmol catalyst Cu( acac) 2 , continue to stir for about 0.5h, then raise the temperature to 70°C, stir for another 6h, and detect the reaction progress by thin-layer chromatography. Add 20mL of ethyl acetate in three times, combine the organic layer, wash the organic layer twice with saturated brine, combine the organic layer, dry over anhydrous sodium sulfate, evaporate the solvent under reduced pressure to obtain a solid, use 95% ethanol as solvent Recrystallization was carried out to obtain the target product with a yield of 92%.

Embodiment 2

[0022] The reaction formula is:

[0023]

[0024] Add 10mmol (5-chloro-1H-indol-3-yl)methanamine, 12mmol 3-butynoic acid and 10mL ionic liquid [HMIm]Cl into the reaction flask, stir until dissolved, then add 0.6mmol catalyst Vo(acac ) 2 , continue to stir for about 0.5h, then raise the temperature to 80°C, stir and react for 8h, and detect the reaction process by thin-layer chromatography. Add 20 mL of ethyl acetate in three times, combine the organic layer, wash the organic layer twice with saturated brine, combine the organic layer, dry over anhydrous sodium sulfate, evaporate the solvent under reduced pressure to obtain a solid, and use 95% ethanol as the solvent for After recrystallization, the target product was obtained with a yield of 86%.

Embodiment 3

[0026] The reaction formula is:

[0027]

[0028] Add 10mmol (5-methoxy-1H-indol-3-yl)methanamine, 12mmol 4-(p-tolyl)-3-butynoic acid and 10mL ionic liquid [BMMIm]Br into the reaction flask, stir to dissolve Then add 0.8mmol catalyst Ni(acac) 2 , continue to stir for about 0.5h, then raise the temperature to 75°C, stir for another 7h, and detect the reaction process by thin-layer chromatography. Add 20mL of ethyl acetate in three times, combine the organic layer, wash the organic layer twice with saturated brine, combine the organic layer, dry over anhydrous sodium sulfate, evaporate the solvent under reduced pressure to obtain a solid, use 95% ethanol as solvent Recrystallization was carried out to obtain the target product with a yield of 80%.

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Abstract

The invention discloses a synthesizing method of indole and indolizine ketone compounds. Chemical equation of the synthesizing method is shown in the description, wherein R1 and R2 represent groups onaromatic rings and nitrogen atoms of 3-indole methylamine compounds respectively, R3 represents groups on triple bonds of 3-tetrolic acid compounds, a catalyst is acetylacetone metal complex, and thegeneral formula of the catalyst is M(acac)2; ionic liquid is [BMIm]X, [PMIm]X, [HMIm]X, [BMMIm]X, [BMMIm]BF4 and [EMIm]BF4. The synthesizing method of the indole and indolizine ketone compounds is novel, easy and efficient.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a method for synthesizing indoloindoxazinone compounds. Background technique [0002] Nitrogen-containing heterocyclic compounds are important organic molecules, which widely exist in medicine, pesticide and material molecules. Indole is an important nitrogen-containing aromatic heterocyclic compound with potential biological activity. It has irreplaceable importance in the synthesis of pharmaceuticals, materials and bioactive molecules. It has become the core structural unit of many drug molecules; indolezine is also a It is an important nitrogen-containing heterocyclic compound, but it is sensitive to light and is easily oxidized in the air to cause ring damage, which limits its application in organic synthesis to a certain extent. However, in recent years, with the development of medicinal chemistry Development, indoxazine derivatives have shown very goo...

Claims

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Application Information

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IPC IPC(8): C07D471/04
Inventor 王启发胡浩强程青芳王丹苏欣宇曹一鸣
Owner HUAIHAI INST OF TECH
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